Oxidative Cleavage of β-Keto Sulfones via Nitrous Acid
Author
Source
Issue
Vol. 2014, Issue 2014 (31 Dec. 2014), pp.1-4, 4 p.
Publisher
Hindawi Publishing Corporation
Publication Date
2014-12-15
Country of Publication
Egypt
No. of Pages
4
Main Subjects
Abstract EN
The reaction of nitrous acid with 1-aryl-2-(arylsulfonyl)ethanones 3a–e afforded the unexpected arenecarboxylic acids 12a–e, formic acid 14, and benzene/4-toluenesulfinic acid 15a, b through oxidative cleavage reaction.
4-Chlorobenzoic acid (12a), [1,1′-biphenyl]-4-carboxylic acid (12b), 2-naphthoic acid (12c), 2-thiophenecarboxylic acid (12d), and 2-benzofurancarboxylic acid (12e) were isolated in 72%, 62%, 55%, 58%, and 62% yields, respectively.
The reported mechanistic pathways proposed the production of 1-aryl-2-(phenyl/tolylsulfonyl)ethane-1,2-dione 7 instead of arenecarboxylic acids 12.
A mechanistic pathway to explain the reaction of nitrous acid with 1-aryl-2-(arylsulfonyl)ethanones 3a–e was suggested.
In this pathway, the intermediate 1,2-oxazete 10 lost benzene/4-toluenesulfinic acid 15 to produce 1,2-oxazet-3-one 11.
Ring cleavage of the latter intermediate afforded the arenecarboxylic acids 12.
American Psychological Association (APA)
Abdel-Aziz, Hatem A.. 2014. Oxidative Cleavage of β-Keto Sulfones via Nitrous Acid. Journal of Chemistry،Vol. 2014, no. 2014, pp.1-4.
https://search.emarefa.net/detail/BIM-1040004
Modern Language Association (MLA)
Abdel-Aziz, Hatem A.. Oxidative Cleavage of β-Keto Sulfones via Nitrous Acid. Journal of Chemistry No. 2014 (2014), pp.1-4.
https://search.emarefa.net/detail/BIM-1040004
American Medical Association (AMA)
Abdel-Aziz, Hatem A.. Oxidative Cleavage of β-Keto Sulfones via Nitrous Acid. Journal of Chemistry. 2014. Vol. 2014, no. 2014, pp.1-4.
https://search.emarefa.net/detail/BIM-1040004
Data Type
Journal Articles
Language
English
Notes
Includes bibliographical references
Record ID
BIM-1040004